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Alkylation of Imidazole-4(5)-carboxylic Acid Derivatives with Methyl Bromoacetate

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Abstract

The alkylation of imidazole-4(5)-carboxylic acid anilide and methyl ester with bromoacetic acid and its methyl ester in neutral and alkaline media yields, along with monoalkylation products, 1,3-bis(2-methoxycarbonylmethyl)-4-R-imidazolium bromide. The monoalkylation of methyl imidazole-4(5)-carboxylate yields a 1:1 mixture of the 1,4- and 1,5-isomers, and the monoalkylation of imidazole-4(5)-carboxylic anilide selectively provides the 1,4-isomer.

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Authors and Affiliations

  1. Research Institute of Experimental Medicine, Russian Academy of Sciences, St. Petersburg, Russia

    M. A. Dumpis, E. V. Litasova & L. B. Piotrovskii

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  1. M. A. Dumpis
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  2. E. M. Alekseeva
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  3. E. V. Litasova
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  4. L. B. Piotrovskii
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Dumpis, M.A., Alekseeva, E.M., Litasova, E.V. et al. Alkylation of Imidazole-4(5)-carboxylic Acid Derivatives with Methyl Bromoacetate. Russian Journal of General Chemistry 73, 126–130 (2003). https://doi.org/10.1023/A:1023447123643

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